20 Questions to Ask Your Partner on a First Date

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a happy couple eating a dessert in street cafe

Whether this is your first date or you have been married for 45 years, relationships and dating are hard AF. When you have been dating for a while, the conversation can begin to turn boring, no one likes talking about the same old topics every time. Sometimes there aren’t even any topics, you’ve exhausted everything to talk about already. And on a first date, oh god a first date. The first few dates are nightmares. What am I going to wear? What if he east onion? Should I shave? What the hell are we going to talk about? Which are the questions to ask a guy you like?

Good Questions to Ask a Guy And Make a Date Much More Interesting

1.What is your favorite memory as a child?
Maybe not for a first date, however, this is something you are likely to not know about someone, and if you don’t ask it will never come up. Also, it is such an important thing. That memory is likely to have shaped the way he is as an adult

2.If you could change one thing about your looks, what would it be?
This can let you know what they are insecure about, or if they are cocky, or even if they are willing to open up to you yet.

3.Which of your parents are you most like?
Not only this but ask why. If you have met their parents you can have a conversation about it. If you haven’t, then you are likely to pick on new characteristics they think they have you hadn’t noticed before.

a happy couples drinking tea in street cafe

4.What’s a new hobby you’d like to try?
You learn about them, AND you get date night ideas. When it comes to questions to ask a guy you like, tip, they love talking about themselves.

5.What was the first thing you thought of me?
This one is one of my favorites because we all want to know this, but probably no one ever asks. Whether he thought you were a thot or it was love, at first sight, it is a nice story to tell your grandchildren.

6.If you won the lottery, what is the first thing you would do?
Now you’ll know who should handle the money in your relationship, you’re welcome. But also, you can take a hint in his dreams and aspirations.

7.How would you describe an ideal day?
Again, date ideas. But also learning more about what he really likes.

8.What’s the happiest you’ve ever felt?
This is such a vague but personal question. The moment someone has felt happiest says a lot about them. They can also say something cheesy about being with you that’ll make you blush and feel like a queen.

a couple drinking wine in restaurant

9.What do you want to do when you retire?
Especially if you’ve been going at it for a while, this is something you want to know. See if what you both want out of life is similar.

10.For what in your life do you feel most grateful?
Because this way you know what things he appreciates out of life. But you can also know what aspects he appreciates of his life with you.

11.If you could meet one famous person, who would it be?
This is a basic and a question we don’t ask enough. Peoples answers can be so varied and unexpected.

12.What’s another career that you think you’d love?
Knowing this about someone can give out a lot. You probably know they like what they do (or they don’t), but what is something else. Be an astronaut? A chef?

13.If you could go back in time, what age would you be?
This will give out what things they appreciate of life, but also on what they feel was a happy time in their lives. This is something you need to know.

14.Are you an optimist, pessimist or realist?
Not really important to cultivate your relationship, in my opinion. But is always good to know how they’ll approach problems.

15.What was your favorite date night you’ve ever had?
If you are married he’ll probably say something with you. If you are not: date night ideas.

a woman with flowers and a man hugging her

16.What’s your biggest regret in life?
Is it something they didn’t do? Does it have to do with you? Is it something they did?

17.If you bought a boat, what would you name it?
Weird question, but knowing they would name it after you will make your week.

18.What fears do you have?
This one is also super personal, but it can let in a lot of things about someone. If you are married they might be about your relationship.

19.If you could live anywhere in the world, where would it be?
It tells you what they want out of life if you think about it.

20.What’s a question you’ve never asked me?
This one is great to break the ice. But also, to get new things into the conversation you’ve been wanting you to get in. It’s one of those good questions to ask a guy.

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